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Phillipston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Phillipston vacation rentals

A house with a stone wall and a dock extending into a calm body of water.

1. Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
$406 nightly
The price is $445
Oct 15 - Oct 16
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

2. Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$468 nightly
The price is $513
Oct 22 - Oct 23
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A house by a lake with a dock and a boat.

3. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
$278 nightly
The price is $302
Oct 20 - Oct 21
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

4. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
$367 nightly
The price is $388
Oct 14 - Oct 15
Total with taxes and fees
Enjoy your stay in an antique home in an antique toy museum!
A cabin with a covered porch, large windows, and snow-covered ground.

5. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
$282 nightly
The price is $306
Oct 14 - Oct 15
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A bedroom with a four-poster bed, wooden flooring, a dresser, a television, and a window with curtains.

6. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
$741 nightly
The price is $783
Nov 8 - Nov 9
Total with taxes and fees
The Christmas Cottage, 4BR New England Escape
A grassy outdoor area with a hammock, chairs, and a stone wall.

7. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$209 nightly
The price is $221
Nov 3 - Nov 4
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (3 reviews)
"The property was adorable, clean and had everything we needed. Even though it rained all weekend we still had the best time. Great, private location with amazing views and close to downtown Keene. The host was very responsive and made sure we were comfortable and had all the info we needed."
United States
Marie M.
$273 nightly
The price is $296
Oct 14 - Oct 15
Total with taxes and fees
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

9. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
$334 nightly
The price is $363
Oct 19 - Oct 20
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A wooden deck with outdoor furniture, a white door, and windows.

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
$361 nightly
The price is $392
Oct 14 - Oct 15
Total with taxes and fees
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A bedroom with a bed, a nightstand, a ceiling fan, and three windows with blinds.

11. Fitchburg hideaway Home

Fitchburg hideaway Home
Fitchburg
$215 nightly
The price is $240
Oct 27 - Oct 28
Total with taxes and fees
Fitchburg hideaway Home
A lakeside park with picnic tables and a concrete walkway.

12. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Oct 14 - Oct 15
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
The Cottage is nestled next to the historic Sagendorph Mansion.

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
$233 nightly
The price is $235
Oct 14 - Oct 15
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
A modern kitchen with a marble island, stainless steel appliances, and bar stools.

14. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
$631 nightly
The price is $704
Oct 14 - Oct 15
Total with taxes and fees
Entire home in Sterling, Massachusetts, United States
A lakeside residential area with houses along the water's edge, a dock, and a boat.

15. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
$700 nightly
The price is $782
Nov 1 - Nov 2
Total with taxes and fees
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

16. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
$534 nightly
The price is $564
Nov 1 - Nov 2
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Phillipston Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"This resort was amazing"
Abderaouf 1-night trip
Posted 5 hours ago
Great Wolf Lodge Boston / Fitchburg, MA

Find out more about Phillipston

Everything you need to know about Phillipston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Phillipston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Phillipston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Phillipston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Phillipston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Phillipston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $219 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Phillipston rentals

At Expedia, we put the best Phillipston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Phillipston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Phillipston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Phillipston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Phillipston?

Yes, we give you a choice of vacation rentals in Phillipston near Red Apple Farm, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Phillipston?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: You might want to consider this vacation home rental near Phillipston, which is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Phillipston?

Family-friendly attractions include Jacobs Hill, whereas Millers River is a spot to enjoy the outdoors. Red Apple Farm and Lake Dennison State Recreation Area are a couple of places you'll find in the larger area.

What’s a vacation rental in Phillipston like?

Vacation rentals are private properties you can stay in for a long or short time in Phillipston. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.